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Exchange 2013 can't connect from Outlook

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Hi,

I am currently migrating Exchange 2007 to 2013 but have run into a strange problem trying to connect from Outlook 2007 or 2010 (haven’t tried 2013). I have spent 3 days trying to solve this now and its driving me crazy now, any advice would be greatly appreciated.

Outlook autodiscover process finds the mailbox but then prompts for a login and then all logins fail even when the correct credientials are definitely being used and the account is not then being locked out. The GUID of the mailbox shown by Outlook is correct.  

can connect to the mailbox fine using OWA.

This is the same for Mailboxes created on Exchange 2013 or migrated to it

I am currently just trying to test Outlook connectivity as I will be swiching all external DNS records to point to EX2013 next week so at the moment all external records point to 2007 whilst all internal DNS records point to 2013.

I am using a wildcard certificate and it has been installed on both servers.

One thing I have noticed is that the ‘Exchangeversion’ is the same on each server which seems like it must be a mistake.

Below is the output from get-outlookanywhere | fl

 

 

RunspaceId                         : 9cff00a7-eb02-4c88-b379-b351c6f8a3f2

ServerName                         : EX2007

SSLOffloading                      : True

ExternalHostname                   : webmail.domain.org.uk

InternalHostname                   : ex2013.domain.org.uk

ExternalClientAuthenticationMethod : Basic

InternalClientAuthenticationMethod : Ntlm

IISAuthenticationMethods           : {Basic, Ntlm, Negotiate}

XropUrl                            :

ExternalClientsRequireSsl          : True

InternalClientsRequireSsl          : True

MetabasePath                       : IIS://ex2007.domain.org.uk/W3SVC/1/ROOT/Rpc

Path                               : C:\Windows\System32\RpcProxy

ExtendedProtectionTokenChecking    : None

ExtendedProtectionFlags            : {}

ExtendedProtectionSPNList          : {}

AdminDisplayVersion                : Version 8.3 (Build 83.6)

Server                             : EX2007

AdminDisplayName                   :

ExchangeVersion                    : 0.1 (8.0.535.0)

Name                               : Rpc (Default Web Site)

DistinguishedName                  : CN=Rpc (Default Web Site),CN=HTTP,CN=Protocols,CN=EX2007,CN=Servers,CN=Exchange

                                     Administrative Group (FYDIBOHF23SPDLT),CN=Administrative

                                     Groups,CN=domain,CN=Microsoft

                                     Exchange,CN=Services,CN=Configuration,DC=domain,DC=org,DC=uk

Identity                           : EX2007\Rpc (Default Web Site)

Guid                               : d482b79a-9b23-4edd-92d7-8e500faea8fa

ObjectCategory                     : domain.org.uk/Configuration/Schema/ms-Exch-Rpc-Http-Virtual-Directory

ObjectClass                        : {top, msExchVirtualDirectory, msExchRpcHttpVirtualDirectory}

WhenChanged                        : 20/01/2015 17:02:08

WhenCreated                        : 01/05/2013 11:51:05

WhenChangedUTC                     : 20/01/2015 17:02:08

WhenCreatedUTC                     : 01/05/2013 10:51:05

OrganizationId                     :

OriginatingServer                  : DC2.domain.org.uk

IsValid                            : True

ObjectState                        : Changed

 

RunspaceId                         : 9cff00a7-eb02-4c88-b379-b351c6f8a3f2

ServerName                         : EX2013

SSLOffloading                      : True

ExternalHostname                   : webmail.domain.org.uk

InternalHostname                   : ex2013.domain.org.uk

ExternalClientAuthenticationMethod : Basic

InternalClientAuthenticationMethod : Ntlm

IISAuthenticationMethods           : {Basic, Ntlm, Negotiate}

XropUrl                            :

ExternalClientsRequireSsl          : True

InternalClientsRequireSsl          : True

MetabasePath                       : IIS://ex2013.domain.org.uk/W3SVC/1/ROOT/Rpc

Path                               : C:\Program Files\Microsoft\Exchange Server\V15\FrontEnd\HttpProxy\rpc

ExtendedProtectionTokenChecking    : None

ExtendedProtectionFlags            : {}

ExtendedProtectionSPNList          : {}

AdminDisplayVersion                : Version 15.0 (Build 847.32)

Server                             : EX2013

AdminDisplayName                   :

ExchangeVersion                    : 0.20 (15.0.0.0)

Name                               : Rpc (Default Web Site)

DistinguishedName                  : CN=Rpc (Default Web Site),CN=HTTP,CN=Protocols,CN=EX2013,CN=Servers,CN=Exchange

                                     Administrative Group (FYDIBOHF23SPDLT),CN=Administrative

                                     Groups,CN=domain,CN=Microsoft

                                     Exchange,CN=Services,CN=Configuration,DC=domain,DC=org,DC=uk

Identity                           : EX2013\Rpc (Default Web Site)

Guid                               : c6293197-0f44-4927-b37a-66bc38742502

ObjectCategory                     : domain.org.uk/Configuration/Schema/ms-Exch-Rpc-Http-Virtual-Directory

ObjectClass                        : {top, msExchVirtualDirectory, msExchRpcHttpVirtualDirectory}

WhenChanged                        : 20/01/2015 17:02:08

WhenCreated                        : 18/12/2014 13:27:50

WhenChangedUTC                     : 20/01/2015 17:02:08

WhenCreatedUTC                     : 18/12/2014 13:27:50

OrganizationId                     :

OriginatingServer                  : DC2.domain.org.uk

IsValid                            : True

ObjectState                        : Changed

 

 

And below is the result of get-outlookprovider | fl (Which also shows the wrong version)

 

 

RunspaceId             : 3e64b3bb-31e8-48a1-946d-45df22a1d679

CertPrincipalName      :

Server                 :

TTL                    : 1

OutlookProviderFlags   : None

RequiredClientVersions :

AdminDisplayName       :

ExchangeVersion        : 0.1 (8.0.535.0)

Name                   : EXCH

DistinguishedName      : CN=EXCH,CN=Outlook,CN=AutoDiscover,CN=Client Access,CN=DOMAIN,CN=Microsoft

                         Exchange,CN=Services,CN=Configuration,DC=domain,DC=org,DC=uk

Identity               : EXCH

Guid                   : 27fbd0f4-7207-4abf-be6d-cd96b8b30a4f

ObjectCategory         : domain.org.uk/Configuration/Schema/ms-Exch-Auto-Discover-Config

ObjectClass            : {top, msExchAutoDiscoverConfig}

WhenChanged            : 16/07/2010 17:29:11

WhenCreated            : 10/07/2008 09:59:43

WhenChangedUTC         : 16/07/2010 16:29:11

WhenCreatedUTC         : 10/07/2008 08:59:43

OrganizationId         :

OriginatingServer      : DC2.domain.org.uk

IsValid                : True

ObjectState            : Unchanged

 

RunspaceId             : 3e64b3bb-31e8-48a1-946d-45df22a1d679

CertPrincipalName      : msstd:webmail.domain.org.uk

Server                 :

TTL                    : 1

OutlookProviderFlags   : None

RequiredClientVersions :

AdminDisplayName       :

ExchangeVersion        : 0.1 (8.0.535.0)

Name                   : EXPR

DistinguishedName      : CN=EXPR,CN=Outlook,CN=AutoDiscover,CN=Client Access,CN=DOMAIN,CN=Microsoft

                         Exchange,CN=Services,CN=Configuration,DC=domain,DC=org,DC=uk

Identity               : EXPR

Guid                   : ce360167-4cb9-4743-9bb6-76638906ca2b

ObjectCategory         : domain.org.uk/Configuration/Schema/ms-Exch-Auto-Discover-Config

ObjectClass            : {top, msExchAutoDiscoverConfig}

WhenChanged            : 21/01/2015 10:42:07

WhenCreated            : 10/07/2008 09:59:43

WhenChangedUTC         : 21/01/2015 10:42:07

WhenCreatedUTC         : 10/07/2008 08:59:43

OrganizationId         :

OriginatingServer      : DC2.domain.org.uk

IsValid                : True

ObjectState            : Unchanged

 

RunspaceId             : 3e64b3bb-31e8-48a1-946d-45df22a1d679

CertPrincipalName      :

Server                 :

TTL                    : 1

OutlookProviderFlags   : None

RequiredClientVersions :

AdminDisplayName       :

ExchangeVersion        : 0.1 (8.0.535.0)

Name                   : WEB

DistinguishedName      : CN=WEB,CN=Outlook,CN=AutoDiscover,CN=Client Access,CN=DOMAIN,CN=Microsoft

                         Exchange,CN=Services,CN=Configuration,DC=domain,DC=org,DC=uk

Identity               : WEB

Guid                   : 5a27fb7b-619c-4da4-9782-3b4bedf775f1

ObjectCategory         : domain.org.uk/Configuration/Schema/ms-Exch-Auto-Discover-Config

ObjectClass            : {top, msExchAutoDiscoverConfig}

WhenChanged            : 16/07/2010 17:29:11

WhenCreated            : 10/07/2008 09:59:43

WhenChangedUTC         : 16/07/2010 16:29:11

WhenCreatedUTC         : 10/07/2008 08:59:43

OrganizationId         :

OriginatingServer      : DC2.domain.org.uk

IsValid                : True

ObjectState            : Unchanged

 

And this is the output of get-exchangeserver

 

 

RunspaceId                      : 3e64b3bb-31e8-48a1-946d-45df22a1d679

Name                            : EX2007

DataPath                        : C:\Program Files\Microsoft\Exchange Server\Mailbox

Domain                          : domain.org.uk

Edition                         : Standard

ExchangeLegacyDN                : /o=DOMAIN/ou=Exchange Administrative Group

                                  (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=EX2007

ExchangeLegacyServerRole        : 0

Fqdn                            : EX2007.domain.org.uk

CustomerFeedbackEnabled         :

InternetWebProxy                :

IsHubTransportServer            : True

IsClientAccessServer            : True

IsExchange2007OrLater           : True

IsEdgeServer                    : False

IsMailboxServer                 : True

IsE14OrLater                    : False

IsE15OrLater                    : False

IsProvisionedServer             : False

IsUnifiedMessagingServer        : False

IsFrontendTransportServer       : False

NetworkAddress                  : {ncacn_vns_spp:EX2007, netbios:EX2007, ncacn_np:EX2007, ncacn_spx:EX2007,

                                  ncacn_ip_tcp:EX2007.domain.org.uk, ncalrpc:EX2007}

OrganizationalUnit              : domain.org.uk/EX2007

AdminDisplayVersion             : Version 8.3 (Build 83.6)

Site                            : domain.org.uk/Configuration/Sites/Default-First-Site-Name

ServerRole                      : Mailbox, ClientAccess, HubTransport

ErrorReportingEnabled           :

StaticDomainControllers         : {}

StaticGlobalCatalogs            : {}

StaticConfigDomainController    :

StaticExcludedDomainControllers : {}

MonitoringGroup                 :

WorkloadManagementPolicy        :

CurrentDomainControllers        : {}

CurrentGlobalCatalogs           : {}

CurrentConfigDomainController   :

ProductID                       : 90559-047-0000007-05612

IsExchangeTrialEdition          : False

IsExpiredExchangeTrialEdition   : False

MailboxProvisioningAttributes   :

RemainingTrialPeriod            : 00:00:00

Identity                        : EX2007

IsValid                         : True

ExchangeVersion                 : 0.1 (8.0.535.0)

DistinguishedName               : CN=EX2007,CN=Servers,CN=Exchange Administrative Group

                                  (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=DOMAIN,CN=Microsoft

                                  Exchange,CN=Services,CN=Configuration,DC=domain,DC=org,DC=uk

Guid                            : f2d1cf56-93c8-4afb-83fa-2149dfe4f30f

ObjectCategory                  : domain.org.uk/Configuration/Schema/ms-Exch-Exchange-Server

ObjectClass                     : {top, server, msExchExchangeServer}

WhenChanged                     : 05/12/2014 20:05:14

WhenCreated                     : 10/07/2008 09:53:59

WhenChangedUTC                  : 05/12/2014 20:05:14

WhenCreatedUTC                  : 10/07/2008 08:53:59

OrganizationId                  :

OriginatingServer               : DC2.domain.org.uk

ObjectState                     : Unchanged

 

RunspaceId                      : 3e64b3bb-31e8-48a1-946d-45df22a1d679

Name                            : EX2013

DataPath                        : C:\Program Files\Microsoft\Exchange Server\V15\Mailbox

Domain                          : domain.org.uk

Edition                         : Enterprise

ExchangeLegacyDN                : /o=DOMAIN/ou=Exchange Administrative Group

                                  (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=EX2013

ExchangeLegacyServerRole        : 0

Fqdn                            : EX2013.domain.org.uk

CustomerFeedbackEnabled         : True

InternetWebProxy                :

IsHubTransportServer            : True

IsClientAccessServer            : True

IsExchange2007OrLater           : True

IsEdgeServer                    : False

IsMailboxServer                 : True

IsE14OrLater                    : True

IsE15OrLater                    : True

IsProvisionedServer             : False

IsUnifiedMessagingServer        : True

IsFrontendTransportServer       : True

NetworkAddress                  : {ncacn_vns_spp:EX2013, netbios:EX2013, ncacn_np:EX2013, ncacn_spx:EX2013,

                                  ncacn_ip_tcp:EX2013.domain.org.uk, ncalrpc:EX2013}

OrganizationalUnit              : domain.org.uk/EX2013

AdminDisplayVersion             : Version 15.0 (Build 847.32)

Site                            : domain.org.uk/Configuration/Sites/Default-First-Site-Name

ServerRole                      : Mailbox, ClientAccess

ErrorReportingEnabled           :

StaticDomainControllers         : {}

StaticGlobalCatalogs            : {}

StaticConfigDomainController    :

StaticExcludedDomainControllers : {}

MonitoringGroup                 :

WorkloadManagementPolicy        : DefaultWorkloadManagementPolicy_15.0.825.0

CurrentDomainControllers        : {}

CurrentGlobalCatalogs           : {}

CurrentConfigDomainController   :

ProductID                       : 02064-004-0073083-02862

IsExchangeTrialEdition          : False

IsExpiredExchangeTrialEdition   : False

MailboxProvisioningAttributes   :

RemainingTrialPeriod            : 00:00:00

Identity                        : EX2013

IsValid                         : True

ExchangeVersion                 : 0.1 (8.0.535.0)

DistinguishedName               : CN=EX2013,CN=Servers,CN=Exchange Administrative Group

                                  (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=DOMAIN,CN=Microsoft

                                  Exchange,CN=Services,CN=Configuration,DC=domain,DC=org,DC=uk

Guid                            : 0acae8de-041c-4a31-8ea8-0b690fdb5e6c

ObjectCategory                  : domain.org.uk/Configuration/Schema/ms-Exch-Exchange-Server

ObjectClass                     : {top, server, msExchExchangeServer}

WhenChanged                     : 07/01/2015 11:39:59

WhenCreated                     : 18/12/2014 13:10:28

WhenChangedUTC                  : 07/01/2015 11:39:59

WhenCreatedUTC                  : 18/12/2014 13:10:28

OrganizationId                  :

OriginatingServer               : DC2.domain.org.uk

ObjectState                     : Unchanged

 

So any ideas? 

 



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